CN101489961A - Electroluminescent polymers and use thereof - Google Patents

Electroluminescent polymers and use thereof Download PDF

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CN101489961A
CN101489961A CNA2007800260149A CN200780026014A CN101489961A CN 101489961 A CN101489961 A CN 101489961A CN A2007800260149 A CNA2007800260149 A CN A2007800260149A CN 200780026014 A CN200780026014 A CN 200780026014A CN 101489961 A CN101489961 A CN 101489961A
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polymkeric substance
carbon atoms
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alkyl chain
radicals
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CN101489961B (en
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阿尔内·比辛
霍尔格·海
奥雷莉·吕德曼
尼尔斯·舒尔特
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Merck Patent GmbH
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Abstract

The invention relates to electroluminescent polymers which contain structural units of formula (I) and to the use of said polymers. The polymers according to the invention have improved efficiency and a longer service-life, especially when used in polymer organic light-emitting diodes.

Description

Electroluminescent polymer and uses thereof
The present invention relates to electroluminescent polymer that comprises general formula (1) structural unit and uses thereof.Polymkeric substance according to the present invention shows improved efficient and longer life-span, particularly when being used for the polymerization Organic Light Emitting Diode.
Demonstration and the research of illumination component wide range of commercial based on polymerization (organic) photodiode (PLEDs) were carried out more than 10 years.This exploitation is to be caused by the foundational development that is disclosed among the WO90/13148 A1.At first, though simple, product (indicating meter that the PHILIPSN.V. shaver is medium and small) also can obtain on market recently.Yet the remarkable improvement of materials used is still necessary, so that these indicating meters become the real rival of the liquid-crystal display (LCDs) in present dominant force market.
In order to make all three kinds of glow colors, be necessary some comonomer is copolymerized in the corresponding polymer (referring to, WO 00/046321 A1 for example, WO 03/020790 A2 and WO 02/077060 A1).In this way, from the coloured light base polymer that turns blue (" skeleton "), might produce other two kinds of primary color red and greens then usually.
The polymkeric substance that is used for panchromatic display element that has proposed or developed is the material of various kinds.Therefore, for example poly-fluorene derivatives and poly-spiral shell two fluorenes, poly-dihydro derivative luxuriant and rich with fragrance and poly-indenofluorene all are suitable.Also proposed to comprise the combination of polymers of described textural element.In addition, use comprises the polymkeric substance of poly(p-phenylene) (PPP) as textural element at present.
Demonstrated good performance when being used for PLEDs in some cases according to prior art polymers.Yet although realized progress, these polymkeric substance can't satisfy makes them be used for the requirement of performance application.
Particularly, green-emitting, the life-span of the coloured light polymkeric substance that especially turns blue is still not enough for many application.The situation of this polymkeric substance that is equally applicable to glow.
Surprisingly, the polymkeric substance of finding a kind of novel kind now has the superperformance that is better than above-mentioned prior art.Therefore the present invention relates to these polymkeric substance and the purposes in PLEDs thereof.This novel structural unit is suitable to especially polymer backbone, but depends on substitution pattern, also can be used as hole conductor, electronic conductor and/or twinkler.
The present invention relates to comprise the unitary polymkeric substance of general formula (1),
Figure A200780026014D00081
General formula (1)
Wherein
R occurs identical or different each time, is H, have 1～40 carbon atom linear alkyl chain, have the branched alkyl chain of 3～40 carbon atoms or have the cyclic alkyl chain of 3～40 carbon atoms, they each can be by R 1Replace, and wherein another one or a plurality of non-adjacent carbon atom can be by=N-R 1,-O-,-S-,-O-CO-O-,-CO-O-,-CR 1=CR 1-or-C ≡ C-substitutes, and wherein another one or a plurality of H atom can be substituted by F, Cl, Br, I or CN, perhaps has the aromatic ring of 5～40 carbon atoms or has the hetero-aromatic ring system of 2～40 carbon atoms, and they can be by one or more radicals R 1Replace; Two radicals R also can form other list or polycyclic fragrance or fatty ring system each other herein; Optimum condition is that at least one or two radicals R are not equal to H;
R 1Occur identical or different each time, be H, have 1～22 carbon atom linear alkyl chain, have the branched alkyl chain of 3～22 carbon atoms or have the cyclic alkyl chain of 3～22 carbon atoms, wherein another one or a plurality of non-adjacent carbon atom can be by=N-R 2,-O-,-S-,-O-CO-O-,-CO-O-,-CR 2=CR 2-or-C ≡ C-substitutes, and wherein another one or a plurality of H atom can be substituted by F, Cl, Br, I or CN, perhaps have aryl, heteroaryl, aryloxy or the heteroaryloxy group of 5～40 carbon atoms, and they can also be by one or more non-aryl R 1Replace; Two or more herein radicals R 1Also can form ring system each other and/or with R; Or F, Cl, Br, I, CN, N (R 2) 2, Si (R 2) 3Or B (R 2) 2
R 2Occurring identical or differently each time, is H or fat or the aromatic hydrocarbon group with 1～20 carbon atom;
X occurs identical or different each time, is B, C, N, O, P, S, Se, P=O, S=O or SO 2
N occurs identical or different each time, is 0,1,2 or 3;
M occurs identical or different each time, is 0,1 or 2; And
Represent link in the polymkeric substance at general formula (1) and the dotted line key in every other general formula.It is not intended to represent methylidene herein.
The present invention preferably relates to and comprises the unitary polymkeric substance of general formula (1a),
General formula (1a)
Wherein
R occurs identical or different each time, is H, have 1～40 carbon atom linear alkyl chain, have the branched alkyl chain of 3～40 carbon atoms or have the cyclic alkyl chain of 3～40 carbon atoms, they each can be by R 1Replace, and wherein another one or a plurality of non-adjacent carbon atom can be by=N-R 1,-O-,-S-,-O-CO-O-,-CO-O-,-CR 1=CR 1-or-C ≡ C-substitutes, and wherein another one or a plurality of H atom can be substituted by F, Cl, Br, I or CN, perhaps has the aromatic ring of 5～40 carbon atoms or has the hetero-aromatic ring system of 2～40 carbon atoms, and they can be by one or more radicals R 1Replace; Two radicals R also can form other list or polycyclic fragrance or fatty ring system each other herein; Optimum condition is that at least one or two radicals R are not equal to H;
R 1Occur identical or different each time, be H, have 1～22 carbon atom linear alkyl chain, have the branched alkyl chain of 3～22 carbon atoms or have the cyclic alkyl chain of 3～22 carbon atoms, wherein another one or a plurality of non-adjacent carbon atom can be by=N-R 2,-O-,-S-,-O-CO-O-,-CO-O-,-CR 2=CR 2-or-C ≡ C-substitutes, and wherein another one or a plurality of H atom can be substituted by F, Cl, Br, I or CN, perhaps have aryl, heteroaryl, aryloxy or the heteroaryloxy group of 5～40 carbon atoms, and they can also be by one or more non-aryl R 1Replace; Two or more herein radicals R 1Also can form ring system each other and/or with R; Or F, Cl, Br, I, CN, N (R 2) 2, Si (R 2) 3Or B (R 2) 2
R 2Occurring identical or differently each time, is H or fat or the aromatic hydrocarbon group with 1～20 carbon atom;
X occurs identical or different each time, is B, C, N, O, P, S, Se, P=O, S=O or SO 2
G occurs identical or different each time, and representative is selected from the 1st group, the 2nd group, the 3rd group, the 4th group, the 5th group, the 6th group, the 7th group or the 1st～7 group of multiple blended divalent unit.
N occurs identical or different each time, is 0,1,2 or 3;
M occurs identical or different each time, is 0,1 or 2;
P occurs identical or different each time, is 0 or 1; And
Represent link in the polymkeric substance at general formula (1a) and the dotted line key in every other general formula; It is not intended to represent methylidene herein.
Although this is apparent from describe, should point out clearly again that general formula (1) and structural unit (1a) can be asymmetrical replacements herein, promptly on a unit, can there be different substituent R or R 1
For the purposes of the present invention, it is the system that there is no need only to comprise respectively fragrance or heteroaryl group that fragrance or hetero-aromatic ring system are defined as looking like, but wherein a plurality of fragrance or heteroaryl group also can be by short non-fragrant unit (＜10% non-H atoms, non-H atom preferably＜5%) is interrupted, such as sp 3The C of-hydridization, O, N etc.Therefore, such as 9,9 '-spiral shell two fluorenes, 9, the 9-diaryl fluorene, systems such as triarylamine, also being defined as the meaning in an application of the invention is aromatic ring.
Usually comprise 5mol% at least according to polymkeric substance of the present invention, preferred 10mol at least, especially preferred 30mol% at least, the particularly general formula of 50mol% (1) or unit (1a) at least.Have been found that: if having different general formula (1) or unit (1a) simultaneously, then general formula (1) and (1a) all unitary summations in above-mentioned scope, make that the content of general formula (1) and single cell (1a) in the case also can be less than 5mol%.
Polymkeric substance according to the present invention is conjugation or partly conjugated polymkeric substance.
For the purposes of the present invention, conjugated polymers is such polymkeric substance: mainly comprise sp in main chain 2The carbon atom of-hydridization, described carbon atom also can be substituted by corresponding heteroatoms.Under the simplest situation, it means on main chain and alternately to have two and singly-bound." mainly " meaning is to cause the natural defect that conjugation is interrupted can not make term " conjugated polymers " invalid.And if for example arylamine units and/or some heterogeneous ring compound (promptly via N, O or S atom conjugation) and/or organometallic complex (promptly via the atoms metal conjugation) are arranged in main chain, the term conjugation is suitable equally in the case.
On the contrary, the unit such as simple alkyl bridged linkage, (sulphur) ether, ester, acid amides or imide link, clearly is defined as non-conjugated segment.Partly conjugated polymkeric substance be defined as looking like be the conjugation segment that wherein in main chain, extends by the intersegmental disconnected polymkeric substance of non-conjugated chain, perhaps wherein be unconjugated and in side chain, comprise the conjugation segmental polymkeric substance of extension in main chain.
Except that general formula (1) or unit (1a), also can comprise other textural elements according to polymkeric substance of the present invention.These are open those that also list in a large number in WO 02/077060 A1 and DE 10337346 A1 especially.These modes by reference are as a part of the present invention.Other structural unit for example can be derived from following kind:
The 1st group: improve the hole injection of polymkeric substance and/or the unit of transport properties;
The 2nd group: improve the electronics injection of polymkeric substance and/or the unit of transport property;
The 3rd group: unit with first group and second group single cell combination;
The 4th group: improve the characteristics of luminescence and reach such degree and make and to obtain electroluminescent phosphorescence but not electroluminescent unit;
The 5th group: improve unit from so-called singlet state to triplet transition;
The 6th group: the polymer morphology that influence obtains and/or the unit of luminous color;
The 7th group: the unit that is used as skeleton usually.
Preferred polymkeric substance is that wherein at least one textural element has those of charge transmission according to the present invention, promptly comprise be derived from the 1st and/or the 2nd group unitary those.
The textural element that is derived from the 1st group has the hole transport characteristic, for example be that triarylamine, p-diaminodiphenyl, four aryl Ursol D, triaryl phosphine, thiodiphenylamine, phenoxazine, dihydrophenazine, thianthrene, dibenzo Dui dioxin, Fen Evil thiophene, carbazole, Azulene, thiophene, pyrroles and furan derivatives and other have the heterocycle that contains O, S or N of high HOMO (HOMO=highest occupied molecular orbital).These arylaminess and heterocycle preferably cause HOMO in the polymkeric substance greater than-5.8ev (relative vacuum energy level), are preferably greater than especially-5.5ev.
The textural element that is derived from the 2nd group has electron transport property, for example be pyridine, pyrimidine, pyridazine, pyrazine, oxadiazole, quinoline, quinoxaline and azophenlyene derivative, and triarylborane have the heterogeneous ring compound that contains O, S or N of low LUMO (LUMO=lowest unoccupied molecular orbital) with other.Unit in these polymkeric substance preferably causes LUMO less than-2.7ev (relative vacuum energy level), especially preferably less than-3.0ev.
Polymkeric substance preferably according to the present invention comprises and is derived from the 3rd group unit, wherein increases the structure of hole mobility and increases structure (promptly being derived from the 1st and the 2nd group unit) the directly combination each other of electronic mobility.These are more unitary to can be used as twinkler and makes glow color change into green, yellow or red.Therefore their purposes for example is suitable for being made by the initial coloured light polymkeric substance that turns blue other glow color.
The 4th group textural element be can in addition at room temperature from luminous expeditiously those of triplet state, promptly show electroluminescent phosphorescence rather than electroluminescent, this causes the raising of energy efficiency usually.At first be suitable for this purpose and be comprising the compound of ordination number greater than 36 heavy atom.Preferably comprise the d that satisfies above-mentioned condition or the compound of f transition metal.Preferably include the corresponding construction unit of the 8th～10 family's element (Ru, Os, Rh, Ir, Pd, Pt) herein especially.The suitable structural unit that herein is used for according to polymkeric substance of the present invention for example is various complex compounds, for example is described among WO02/068435 A1, DE 10116962 A1, EP 1239526 A2 and DE 10238903 A1.Corresponding monomer is described among WO 02/068435 A1 and DE 10350606 A1.
The textural element that is derived from the 5th group is to improve from singlet to the triplet state transition those, can be used for supporting the 4th group textural element, improves the phosphorescent characteristics of these textural elements.Be suitable for this purpose particularly carbazole and bridging carbazole dimerization unit, as described at DE 10304819 A1 and DE 10328627 A1.What also be suitable for this purpose is compounds such as ketone, phosphine oxide, sulfoxide, as describing in DE 10349033.
Be derived from the form and/or the glow color of the 6th group textural element impact polymer, except that aforesaid those, be to have at least one other fragrance or other conjugated structures but do not belong to those of above-mentioned group, promptly, charge carrier mobility is only had very little influence, is not organometallic complex or to singlet-triplet transition those of influence not.The form and/or the glow color of the polymkeric substance that the textural element influence of the type obtains.Depend on described unit, so they can also be used as twinkler.The aromatic structure that preferably has 6～40 carbon atoms herein, the perhaps derivative of tolane, toluylene or diphenylethyllene arylidene, they each can be by one or more radicals R 1Replace.Especially preferably incorporate 1 into herein, 4-phenylene, 1,4-naphthylidene, 1,4-or 9,10-anthrylene, 1,6-, 2,7-or 4, the inferior pyrenyl, 3 of 9-, 9-or 3, the inferior perylene, 4,4 of 10-'-biphenylene, 4,4 ＂-Ya terphenyl, 4,4 '-Ya-1,1 '-binaphthylyl, 4,4 '-Ya tolane base, 4,4 '-Ya stilbene radicals or 4,4 ＂-diphenylethyllene arylene derivatives.
The textural element that is derived from the 7th group be usually as polymer backbone, comprise unit with 6～40 carbon atoms fragrance structures.These for example are 4,5-dihydropyrene derivative, 4,5,9,10-tetrahydrochysene pyrene derivatives, fluorene derivatives, 9,9 '-spirobifluorene derivative, 9,10-dihydro phenanthrene derivative, 5,7-dihydro-dibenzo oxa-
Figure A200780026014D0013132802QIETU
Derivative, and indenofluorene derivative cis and trans.Yet general formula (1) or (1a) unitary ratio are in particular 50mol% at least, and these textural elements that are derived from the 7th group are not preferably used as main polymer backbone herein, but at most to be present in the skeleton than small proportion.
The preferred polymkeric substance according to the present invention except that general formula (1) or structural unit (1a), comprises that also more than one are selected from the 1st～7 group unit simultaneously in addition.Same preferred exist simultaneously be derived from one group more than a kind of structural unit.
General formula (1) or (1a) unitary ratio preferably be at least 10mol%, especially preferably be at least 30mol% and particularly be at least 50mol%.If general formula (1) or unit (1a) they are polymer backbones, this preferred particularly suitable.Under other function situations, other ratios can be preferred, and for example in electroluminescent polymer under the situation of hole conductor or twinkler, ratio is about 5～20mol%.For other application, for example be used for organic transistor, described preferred ratio also can be different, for example under hole or the unitary situation of electronic conduction, can be up to 100mol%.
According to polymkeric substance of the present invention, preferably except that general formula (1) or structural unit (1a), also comprise at least a structural unit that is derived from above-mentioned category.At least two kinds of special preferred sources of structural unit are from above-mentioned those different sorts.If exist, the ratio of these structural units preferably is at least 5mol% under each situation, be preferably 10mol% at least under each situation especially.Especially, one of these structural units are selected from the group of unitary group of hole-conductive and other luminescence units, and wherein these two kinds of functions (hole-conductive is with luminous) also can be born by identical unit.
Yet, for example for synthetic white luminous multipolymer, luminescence unit, particularly green and emitting red light is unitary also can be preferred than small proportion.The method of the synthetic coloured light multipolymer that turns white is described in detail among DE 10343606 A1.
Polymkeric substance of the present invention preferably has 10～10,000, and is preferred especially 50～5000, particularly 50～2000 repeating units.
Especially by at general formula (1) or (1a) on the unit, and choose substituent R and R on the unit of other existence wantonly 1, guarantee the solubleness that polymkeric substance needs.If there is other substituting group, these substituting groups also can promote solubleness.
For guaranteeing enough solubleness, preferred average at least 2 non-fragrant C atoms that in the substituting group of each repeating unit, exist.Preferably at least 4 herein, especially preferred at least 8 C atoms.Its single carbon atom also can be substituted by O or S.Yet, for this repeating unit that might mean some ratio fully any other non-aromatic substituent of carrier band not.
For avoiding damaging the form of film, preferably in linear chain, there is not long-chain substituting group more than 12 C atoms, preferred especially not more than 8 C atoms, particularly there is not long-chain substituting group more than 6 C atoms.
Non-fragrant C atom for example resembles at general formula (1) or R (1a) and R 1Description in, be present in corresponding straight chain, branching or cyclic alkyl or the oxyalkyl chain.
Preferably according to polymkeric substance of the present invention, wherein for general formula (1) or unit (1a),
R occurs identical or different each time, expression have 1～25 carbon atom linear alkyl chain, have the branched alkyl chain of 3～25 carbon atoms or have the cyclic alkyl chain of 3～25 carbon atoms, wherein another one or a plurality of non-adjacent carbon atom can be by=N-R 1,-O-,-S-,-O-CO-O-,-CO-O-,-CH=CH-or-C ≡ C-replaces, and wherein another one or a plurality of H atom can be substituted by F or CN, perhaps have the aromatic ring of 5～20 carbon atoms or have the hetero-aromatic ring system of 2～20 carbon atoms, they can be by one or more non-aryl R 1Replace; Two radicals R also can form other list or polycyclic fragrance or fatty ring system each other herein;
R 1Occur identical or different each time, expression H, have 1～22 carbon atom linear alkyl chain, have the branched alkyl chain of 3～22 carbon atoms or have the cyclic alkyl chain of 3～22 carbon atoms, wherein another one or a plurality of non-adjacent carbon atom can be by=N-R 2,-O-,-S-,-O-CO-O-,-CO-O-,-CH=CH-or-C ≡ C-substitutes, and wherein another one or a plurality of H atom can be substituted by F or CN, the aryl, heteroaryl, aryloxy or the heteroaryloxy group that perhaps have 5～40 carbon atoms, they can also be by one or more non-aryl R 1Replace; Two or more herein radicals R 1Also can form list or polycyclic fat or aromatic ring each other and/or with R; Or F, Cl, Br, I, CN, N (R 2) 2, Si (R 2) 3Or B (R 2) 2And
X occurs identical or different each time, is B, C, N, O, P, S, P=O, S=O or SO 2
Preferably according to polymkeric substance of the present invention, wherein for general formula (1) or unit (1a),
R occurs identical or different each time, is straight chain, branching or the cyclic alkyl chain with 4～20 carbon atoms, special preferred branched alkyl chain, and wherein another one or a plurality of non-adjacent carbon atom can be by=N-R 1,-O-,-S-,-O-CO-O-,-CO-O-,-CH=CH-or-C ≡ C-substitutes, wherein another one or a plurality of H atom can be substituted by F; Two radicals R also can form other list each other or encircle ring system more herein;
It is C that X occurs each time; And
P represents numeral 0.
Aliphatic group R preferably can explain like this: the polymkeric substance that obtains also has better solvability and better synthetic availability.
Depend on substitute mode, general formula (1) or unit (1a) are particularly suitable for the various functions in the polymkeric substance.Therefore, these unit can be preferably used as (electronic conduction) polymer backbone, as hole conductor or as twinkler.
And preferably 7,7 '-general formula (1) or unit (1a) that the position symmetry replaces.This preferably can be explained by the better synthetic availability of this monomer.Therefore, for general formula (1) or (1a) in the unit all R preferably identical, especially preferably also replaced in the same manner.
General formula (1) or (1a) example of preferred cell be following structure, wherein under each situation the link in the polymkeric substance shown in dotted line key via 3, the 9-position takes place.For clarity sake, possible substituting group is not shown usually or be not all to illustrate in each place.As the description for R, alkyl is represented fatty alkyl usually herein, and aryl is represented fragrance or heteroaromatic system.
Figure A200780026014D00171
According to polymkeric substance of the present invention or homopolymer or multipolymer.Except general formula (1) or one or more structures (1a), can choose wantonly according to multipolymer of the present invention and to comprise one or more other structures, those in for example above-mentioned the 1st～7 group.
Can have random, alternative or block-wise structure according to multipolymer of the present invention, perhaps also have a plurality of these structures of alternately arranging.The method that the energy acquisition has the block-wise structure copolymer for example is described in detail among DE 10337077 A1.This does not examine the part that disclosed specification sheets becomes the application by reference.
Can regulate these performances such as solvability, solid phase form, color, electric charge injection and transport property, temperature stability, electro-optical characteristic or the like by using multiple different textural element.
Usually by the monomer preparation of one or more types of polymerization, wherein at least a monomer obtains described polymkeric substance general formula (1) or unit (1a) according to polymkeric substance of the present invention.The polyreaction that many correspondences are arranged in principle.Yet some types that obtain C-C or C-N link here are proved to be successful especially:
(A) SUZUKI polymerization;
(B) YAMAMOTO polymerization;
(C) STILLE polymerization;
(D) HARTWIG-BUCHWALD polymerization.
Can carry out the polymeric mode by these methods, and for example can be described in detail in from the mode of reaction medium isolating polymer and purifying DE 10249723 A1.
The monomer that obtains polymkeric substance formula of (1) structural unit according to the present invention is 3, and the 9-position has suitable functional group, makes this monomeric unit can incorporate the derivative in the polymkeric substance into.If wish other link, then must correspondingly change functional group.
Obtain this polymkeric substance formula of (1) or (1a) unitary monomer be novel, therefore be theme of the present invention equally.
Therefore, the invention further relates to general formula (2) or difunctional monomer compound (2a).
Figure A200780026014D00191
General formula (2)
Figure A200780026014D00201
General formula (2a)
It is characterized in that two functional group A are identical or different, and copolymerization under C-C or C-N link reaction conditions, wherein other symbols and mark have and general formula (1) or (1a) identical implication.
A is preferably selected from Cl, Br, I, O-tosylate, O-triflate, O-SO 2R 2, B (OR 2) 2And Sn (R 2) 3, be preferably selected from Br especially, I and B (OR 2) 2, R wherein 2Has identical as mentioned above implication, wherein two or more radicals R 2Also can form ring system each other.
Described C-C link reaction is preferably selected from SUZUKI coupling, YAMAMOTO coupling and STILLE coupling; Described C-N link reaction is preferably the HARTWIG-BUCHWALD coupling.
As mentioned above for general formula (1) or (1a) structural unit identical preferably be applicable to general formula (2) or difunctional monomer compound (2a).
Preferably do not use polymkeric substance according to the present invention as pure substance, but as the mixture (blend) with other any desired polymeric, oligomeric, dendritic or low-molecular-weight material.These for example can improve Electronic Performance, and the transition of influence from the singlet state to the triplet state or they itself are from singlet state or luminous from triplet state.Yet electronics inert material also can be suitable, for example for the form of the polymeric film that influences formation or the viscosity of polymers soln.Therefore the invention still further relates to the blend of the type.
The invention still further relates to solution and the preparation in one or more solvents according to one or more polymkeric substance of the present invention or blend.The mode that can prepare polymers soln for example be described in WO0 2/072714 A1, WO 03/019694 A2 and the document quoted therein in.These solution can be used for producing thin polymer layer, for example by surface coating process (for example spin coating) or typography (for example ink jet printing).
Can be used among the PLEDs according to polymkeric substance of the present invention.These comprise negative electrode, anode, luminescent layer and other optional layers, such as preferred hole injection layer with choose middle layer between hole injection layer and luminescent layer wantonly.Can produce the method for PLEDs, be described in detail among DE 10304819 A1 as usual method, it should correspondingly be adapted to the discrete situation.
Aforesaid, be particularly suitable as very much the PLEDs that produces in this mode or the electroluminescent material in the indicating meter according to polymkeric substance of the present invention.
For the purposes of the present invention, electroluminescent material is considered to be meant the material that can be used as the active coating among the PLED.The active coating meaning is layer (luminescent layer) luminous when applying electric field and/or just improves and/or negative charge injects and/or the layer of transmission (electric charge injects or charge transport layer).It can also be the middle layer between hole injection layer and luminescent layer.
Therefore the invention still further relates to the purposes of polymkeric substance according to the present invention in PLED, particularly as the purposes of electroluminescent material.
Therefore, the present invention relates to the PLED with one or more active coatings equally, and wherein one of these active coatings comprise that one or more are according to polymkeric substance of the present invention at least.This active coating for example can be luminescent layer and/or transport layer and/or electric charge injection layer and/or middle layer.
Polymkeric substance according to the present invention has following surprising advantage, has surpassed at this as poly-spiral shell two fluorenes and the poly-fluorenes described near WO 03/020790 A2 of prior art and WO 02/077060 A1:
(1) has been found that according to polymkeric substance of the present invention (and other identical or similar compositions) in application, to have higher luminous efficiency.This is specially adapted to show the multipolymer of blue-light-emitting.This is very important, because like this can be in the brightness identical than realization under the lower power intake, this be very important in the mobile application (indicating meter of mobile telephone, beeper, PDAs or the like) of dependence standard or rechargeable cell particularly.On the contrary, can obtain higher brightness with identical energy expenditure, this for example uses for illumination is attracting.
Find surprisingly once more in this external direct comparison that (2) polymkeric substance according to the present invention has longer work-ing life, particularly under the situation of the green-emitting and the PLEDs of the coloured light that turns blue.
(3) even do not use the comonomer of electronic conduction, also be the good electron conductor according to polymkeric substance of the present invention.Because the many electronic conductors according to prior art are stable inadequately for performance application, thereby be difficult to realize the electronic conduction performance of polymkeric substance so far.
The present patent application text and following embodiment relate to the purposes in PLEDs and respective display according to polymkeric substance of the present invention or blend.Although it is limited describing, but for those of ordinary skills, do not need other creative works, polymkeric substance according to the present invention can be used in other purposes in other electron devices equally, these other electron devices are for example only mentioned some application: organic integration circuit (O-ICs), organic field effect tube (OFETs), OTFT (OTFTs), organic solar batteries (O-SCs) or organic laser diode (O-lasers).
The application relates to the purposes of polymkeric substance according to the present invention in corresponding device and these devices itself equally.
Below reference example is illustrated the present invention in further detail in more detail, but is not restricted to this.
Embodiment:
Embodiment 1: preparation 3,9-two bromo-7,7-dimethyl-7H-benzo [de] anthracene
Figure A200780026014D00231
1.1 prepare 3,9-dibromo benzo [de] anthracene-7-ketone
Figure A200780026014D00232
The benzanthrone of 50g (217mmol) is at first introduced in the oil of mirbane of 800ml, made internal temperature reach 90 ℃.Within 30 minutes, dropwise add the bromine that is dissolved in the 25ml (490mmol) in the 100ml oil of mirbane.This reaction mixture is heated to 150 ℃ internal temperature then.After 2 hours, with this mixture cool to room temperature, dropwise add the EtOH of 200ml, go out yellow mercury oxide with suction filtration, with a large amount of EtOH washings, drying obtains the dibrominated product of 49.7g (59%) as yellow powder.
1.2 prepare 3,9-two bromo-7H-benzo [de] anthracenes
Figure A200780026014D00233
With the dibromo benzanthrone of 37.17g (81.7mmol) and the AlCl of 10.9g (81.7mmol) 3At N 2At first introduce down by in the 330ml exsiccant ether in the equipment of heat drying.Then at ice-cooled 3.1g (81.7mmol) LiAlH that dropwise is added in down in the 400ml ether 4(in advance at ice-cooled, N 2Following dissolving or suspension).When adding is finished, with this mixture heating up to 60 minutes that seethe with excitement other.
The ethyl acetate that slowly adds 10ml under ice-cooled situation dropwise adds the 6M HCl of 100ml subsequently carefully, and with the precipitation that suction filtration goes out to obtain, HCl and methanol wash with 1M by suction dried, obtain the faint yellow solid of 25.6g (84%).
1.3 prepare 3,9-two bromo-7,7-dimethyl-7H-benzo [de] anthracene
Figure A200780026014D00241
With 3 of 26g (69mmol), 9-two bromo-7H-benzo [de] anthracenes are dissolved under 70 ℃ among the 280ml exsiccant DMSO, add the NaO of 40g (416mmol) tBu heats the internal temperature of this suspensoid to 80 ℃.The methyl-iodide (1 hour, temperature＜90 ℃) that under this temperature, slowly dropwise adds 25.9ml (416mmol).Then, this internal temperature was kept other 1.5 hours down at 80～90 ℃.This refrigerative batch of material is poured in the frozen water of 1000ml, stirs this mixture 20 minutes, the solid that suction filtration goes out to obtain, water and methanol wash from toluene recrystallization six times, obtain faint yellow solid, productive rate 77% (21.4g), purity〉99.9%.
Embodiment 2: synthetic other monomers
In the synthetic WO of being described in 03/020790 of monomer M 2～M5 as described below in addition and the document of being quoted therein.
Monomer M 2 monomer M 3
Figure A200780026014D00251
Monomer M 4 monomer M 5
Embodiment 3: synthetic polymer
Described in WO 03/048225, synthetic according to polymkeric substance of the present invention and polymkeric substance relatively by the SUZUKI coupling.The composition of synthetic polymer P 1 and P2 and polymkeric substance C1 relatively and the composition of C2 indicate in table 1 according to the present invention.Polymkeric substance C1 relatively and C2 have the monomer different with monomer M 1, and it obtains the unit of polymkeric substance formula of (1).
The manufacturing of embodiment 4:PLEDs
The purposes of research polymkeric substance in PLEDs.This PLEDs is two coating systems under each situation, promptly base material //ITO//PEDOT//polymkeric substance // negative electrode.PEDOT is polythiofuran derivative (from H.C.Starck, Goslar obtains Baytron P).Negative electrode in all situations is Ba/Ag (Aldrich).The method of producing OLEDs be described in detail in WO 04/037887 and the document quoted therein in.
Embodiment 5～8: device embodiment
In PLEDs, use the result who obtains according to polymer P 1 of the present invention and P2 to be shown in the table 1 equally.Also demonstrate the electroluminescent result who uses polymkeric substance C1 relatively and C2 to obtain.
As from the result as seen, better according to the efficient of the efficiency ratio of polymkeric substance of the present invention polymkeric substance relatively.Glow color is comparable, and the life-span significantly improves when considering this factor.This demonstrates polymkeric substance according to the present invention and more is applicable in the indicating meter than prior art polymers.
Table 1:
Embodiment Polymkeric substance Monomer Maximum efficiency/cd/A U@100 cd/m 2/V CIE x/y a Life-span b/ hour
5 P1 10％M150％M220％M310％M410％M5 7.7 2.8 0.16/0.24 400
6 P2 2％M1 50％M246％M32％M5 6.02 3.3 0.15/0.19 1200
7 C1 50％M230％M310％M410％M5 4.66 3.9 0.17/0.30 180
8 C2 50％M246％M32％M4 2％M5 4.70 4.7 0.17/0.26 449
aCIE coordinate: the color coordinate of The Commission Internationale de l ' Eclairage (international lighting association) 1931
bLife-span: the time when brightness drops to original intensity 50%, original intensity is 400cd/m 2

Claims (22)

1. polymkeric substance, it comprises the unit of general formula (1),
Figure A200780026014C00021
General formula (1)
Wherein
R occurs identical or different each time, is H, have 1～40 carbon atom linear alkyl chain, have the branched alkyl chain of 3～40 carbon atoms or have the cyclic alkyl chain of 3～40 carbon atoms, they each can be by R 1Replace, and wherein another one or a plurality of non-adjacent carbon atom can be by=N-R 1,-O-,-S-,-O-CO-O-,-CO-O-,-CR 1=CR 1-or-C ≡ C-substitutes, and wherein another one or a plurality of H atom can be substituted by F, Cl, Br, I or CN, perhaps has the aromatic ring of 5～40 carbon atoms or has the hetero-aromatic ring system of 2～40 carbon atoms, and they can be by one or more radicals R 1Replace; Two radicals R also can form other list or polycyclic fragrance or fatty ring system each other herein; Optimum condition is that at least one or two radicals R are not equal to H;
R 1Occur identical or different each time, be H, have 1～22 carbon atom linear alkyl chain, have the branched alkyl chain of 3～22 carbon atoms or have the cyclic alkyl chain of 3～22 carbon atoms, wherein another one or a plurality of non-adjacent carbon atom can be by=N-R 2,-O-,-S-,-O-CO-O-,-CO-O-,-CR 2=CR 2-or-C ≡ C-substitutes, and wherein another one or a plurality of H atom can be substituted by F, Cl, Br, I or CN, perhaps have aryl, heteroaryl, aryloxy or the heteroaryloxy group of 5～40 carbon atoms, and they can also be by one or more non-aryl R 1Replace; Two or more herein radicals R 1Also can form ring system each other and/or with R; Or F, Cl, Br, I, CN, N (R 2) 2, Si (R 2) 3Or B (R 2) 2
R 2Occurring identical or differently each time, is H or fat or the aromatic hydrocarbon group with 1～20 carbon atom;
X occurs identical or different each time, is B, C, N, O, P, S, Se, P=O, S=O or SO 2
N occurs identical or different each time, is 0,1,2 or 3;
M occurs identical or different each time, is 0,1 or 2; And
Dotted line key is represented the link in the polymkeric substance herein.
2. according to the polymkeric substance of claim 1, it is characterized in that they are conjugation or partly conjugated polymkeric substance.
3. according to the polymkeric substance of claim 1 or 2, it is characterized in that except that the unit of general formula (1), they comprise other textural elements.
4. according to the polymkeric substance of claim 3, it is characterized in that to improve that the hole is injected and/or described other textural elements of transport property are selected from triarylamine, p-diaminodiphenyl, four aryl Ursol D, triaryl phosphine, thiodiphenylamine, phenoxazine, dihydrophenazine, thianthrene, dibenzo Dui dioxin, Fen Evil thiophene, carbazole, Azulene, thiophene, pyrroles and furan derivatives and other have the heterocycle that contains O, S or N of high HOMO.
5. according to claim 3 and 4 at least one s' polymkeric substance, it is characterized in that described other textural elements that increase electronics injection and/or transport property are selected from pyridine, pyrimidine, pyridazine, pyrazine, oxadiazole, quinoline, quinoxaline and azophenlyene derivative, and triarylborane has the heterocycle that contains O, S or N of low LUMO with other.
6. according at least one polymkeric substance of claim 3～5, it is characterized in that described other textural elements have the combination according to the single cell of claim 4 and 5.
7. according at least one polymkeric substance of claim 3～6, it is characterized in that described other textural elements change the characteristics of luminescence to such degree, make it possible to obtain electroluminescent phosphorescence but not electroluminescent.
8. according at least one polymkeric substance of claim 3～7, described other textural elements that it is characterized in that improving from the singlet state to the triplet transition are selected from carbazole and bridging carbazole dimerization unit, ketone, phosphine oxide, sulfoxide, sulfone and silane derivative.
9. according at least one polymkeric substance of claim 3～8, described other textural elements that it is characterized in that impact polymer form and/or glow color are selected from 1,4-phenylene, 1,4-naphthylidene, 1,4-or 9,10-anthrylene, 1,6-, 2,7-or 4, the inferior pyrenyl, 3 of 9-, 9-or 3, the inferior perylene, 4 of 10-, 4 '-biphenylene, 4,4 ＂-Ya terphenyl, 4,4 '-Ya-1,1 '-binaphthylyl, 4,4 '-Ya tolane base, 4,4 '-Ya stilbene radicals or 4,4 ＂-diphenylethyllene arylene derivatives.
10. according to the polymkeric substance of at least one of claim 3～9, it is characterized in that described other textural elements that are used as skeleton usually are selected from 4,5-dihydropyrene derivative, 4,5,9,10-tetrahydrochysene pyrene derivatives, fluorene derivatives, 9,9 '-spirobifluorene derivative, 9,10-dihydro phenanthrene derivative, 5,7-dihydro-dibenzo oxa-
Figure A200780026014C0004095558QIETU
Indenofluorene derivative derivative and cis and trans.
11., it is characterized in that the unitary ratio of general formula (1) is 5mol% at least according to the polymkeric substance of at least one of claim 1～10.
12. according to the polymkeric substance of at least one of claim 1～11, the unit that it is characterized in that general formula (1) is via 3, the 9-link is combined in the polymkeric substance.
13. the polymkeric substance according at least one of claim 1～12 is characterized in that, in general formula (1),
R occurs identical or different each time, representative have 1～25 carbon atom linear alkyl chain, have the branched alkyl chain of 3～25 carbon atoms or have the cyclic alkyl chain of 3～25 carbon atoms, wherein another one or a plurality of non-adjacent carbon atom can be by=N-R 1,-O-,-S-,-O-CO-O-,-CO-O-,-CH=CH-or-C ≡ C-substitutes, and wherein another one or a plurality of H atom can be substituted by F or CN, perhaps have the fragrance or the heteroaryl group of 4～20 carbon atoms, they can be by one or more non-aryl R 1Replace; Two radicals R also can form other list or polycyclic fragrance or fatty ring system each other herein;
R 1Occur identical or differently each time, represent H, have 1～22 carbon atom linear alkyl chain, have the branched alkyl chain of 3～22 carbon atoms or have the cyclic alkyl chain of 3～22 carbon atoms, wherein another one or a plurality of non-adjacent C atom can be by=N-R 2,-O-,-S-,-O-CO-O-,-CO-O-,-CH=CH-or-C ≡ C-substitutes, and wherein another one or a plurality of H atom can be substituted by F or CN, the aryl, heteroaryl, aryloxy or the heteroaryloxy that perhaps have 5～40 carbon atoms, they can also be by one or more non-aryl R 1Replace; Two or more herein radicals R 1Also can form list or polycyclic fat or aromatic ring each other and/or with R; Or F, Cl, Br, I, CN, N (R 2) 2, Si (R 2) 3Or B (R 2) 2And
X occurs identical or different each time, represents B, C, N, O, P, S, P=O, S=O or SO 2
14. the difunctional monomer compound of a general formula (2),
Figure A200780026014C00051
General formula (2)
It is characterized in that two functional group A are identical or different, and copolymerization under C-C or C-N link reaction conditions; And other symbols and label are just like implication identical shown in the claim 1.
15. the difunctional monomer compound according to the general formula (2) of claim 14 is characterized in that A is selected from Cl, Br, I, O-tosylate, O-triflate, O-SO 2R 2, B (OR 2) 2And Sn (R 2) 3, R wherein 2Has implication identical shown in claim 1, wherein two or more radicals R 2Also can form ring system each other.
16. difunctional monomer compound according to the general formula (2) of claim 14 or 15, it is characterized in that described C-C link reaction is selected from SUZUKI coupling, YAMAMOTO coupling and STILLE coupling, be characterised in that perhaps described C-N link reaction is the HARTWIG-BUCHWALD coupling.
17. mixture (blend) according to one or more polymkeric substance of at least one of claim 1～13 and other polymeric, oligomeric, dendritic and/or low-molecular-weight material.
18. one kind according to one or more polymkeric substance of at least one of claim 1～13 or according to solution and the preparation of blend in one or more solvents of claim 17.
19. according to the polymkeric substance of at least one of claim 1～13, according to the blend of claim 17 or according to the purposes of solution in photodiode of claim 18.
20. the organic electronic assembly with one or more active coatings, at least one that it is characterized in that these active coatings comprise according to one or more polymkeric substance of at least one of claim 1～13 or according to the blend of claim 17.
21., it is characterized in that it is polymer LED (PLED), organic integration circuit (O-IC), organic field effect tube (OFET), OTFT (OTFT), organic solar batteries (O-SC) or organic laser diode (O-laser) according to the organic electronic assembly of claim 20.
22., it is characterized in that it is a polymer LED according to the organic electronic assembly of claim 21.
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